Wednesday, July 16, 2008

On the Street…..Shorts & Jacket, Milan

A shorts suit? Doesn’t work for me.

Shorts and a sportscoat? Just right.


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  1. Anonymous

    July 16, 2008 at 9:38 am

    love the shoes on the first guy

  2. lintmag

    July 16, 2008 at 9:43 am

    I agree with you – no shorts suits – too boarding school boy looking! These men all look really great, except for the shoes – there must be some better choice. Also, I love that necklace on the woman in the bottom photo.

  3. Jorge from W Palm Beach

    July 16, 2008 at 9:47 am

    Agree- I truly can’t think of a single occasion in which a grown man can really pull off a suit with shorts. All 3 examples you show are soft construction jackets which look good when slightly rumpled. For us in South Florida, sometimes it is necessary to wear just the shirt outside and then throw your jacket on when you enter chilled buildings, and it makes for a nice evening look if you stay out past sundown. I like to buy JCrew’s chino jackets (when they go on sale) and other unlined linen or cotton blazers, and those seem to do the trick. Jorge from W Palm Beach

  4. Iheartfashion

    July 16, 2008 at 10:11 am

    Yes, a matching shorts suit is a bit too Little Lord Fauntleroy. Very cute on a 5-year old.
    But I love the rumpled sport coat with shorts, worn in a casual way.

  5. Anonymous

    July 16, 2008 at 10:19 am

    The Asian gentleman has done an exquisite job updating the traditional outfit of Bermuda. Still, I’d like to see the button-down buttoned-down.

  6. Dan

    July 16, 2008 at 10:20 am

    The first two look great, while embodying such completely different styles. I wouldn’t wear either of these ensembles, but both suit their respective wearers beautifully. I will work on my own combination, though, after being inspired here.
    Number three I find too disjointed and looking too carelessly thrown together- the belt (a little sloppy), the cuffs on too-tight shorts, inappropriate-looking shoes.

  7. Max

    July 16, 2008 at 10:31 am

    The first guy looks great. Is that a three button jacket rolled to two? The second one looks really boring in my opinion: rather the sort of look you see on every Tom, Dick and Harry in Hyde Park when it’s sunny. The bottom one has all the right attributes but I think something about the fit of the shorts makes the look a bit uptight.

  8. S

    July 16, 2008 at 11:02 am

    The man in the first picture is ridiculously dapper looking. And the photo is very beautiful – the soft light is perfect.

  9. Diederik

    July 16, 2008 at 11:24 am

    Jackets on shorts I just can’t take seriously unless you are a government official in Bermuda.

    By the way, what’s with all these unbuttoned sleeves I see appearing in this blog (and elsewhere). It is such ungentlemanly behaviour.

  10. The Domina

    July 16, 2008 at 11:25 am

    Short suits are just awful and I think it takes a certain type of flair and body shape to pull off shorts with a jacket…the first and second one are great but there is something about the shoes in the third that is throwing the entire look off for me.

  11. Carolina Lange

    July 16, 2008 at 11:26 am

    They look great!

  12. [mega] Paulo Mamedes

    July 16, 2008 at 11:36 am

    These two pieces definetely don’t match!

    Até no Brasil tentaram emplacar esse look, acho que não vai rolar nunca!

  13. tj

    July 16, 2008 at 11:40 am

    I think the top outfit looks confused. The low-riding shorts don’t seem to work well with the classier shirt and jacket.
    But, the bottom two are both great. Middle photo is casual and relaxed, bottom photo is a more of a business-look. I’d have gone with a more casual shoe in the bottom photo to better match the casual belt, but the jacket (is it seersucker?) works great with the shirt and shorts.

  14. K.B.

    July 16, 2008 at 12:01 pm

    Not crazy about the striped jacket in the first picture, but the unbuttoned white jackets are fine. I’m still deciding if I like this look or not. In the office, probably not, but on the street when temperatures are roasting, yeah, probably.

  15. Greg in Boston

    July 16, 2008 at 12:04 pm

    Hi all,

    I have a naive question: How does someone go about finding wardrobe elements in an intentional way?

    I’ve been enjoying this blog for a few weeks now, and have seen some stylistic ideas that I’d like to incorporate into my wardrobe, but I realize that I don’t know where to go to find nicely cut lightweight summer sportscoats, etc.

    I’m not looking for a shopping list, but really for some thoughts on how a person would assemble his own shopping list.

    (Is finding a good tailor the answer? I fear that that’s the answer.)

    Thanks for your thoughts – I’ve been enjoying the posts on this list quite a lot.


  16. TheSmiterOfTim

    July 16, 2008 at 12:21 pm

    Are these three short men, or does this look just sort of give a ‘shortened’ stature? I was thinking of suggesting it to some guys and then I started wondering if it would make them look shorter: probably not the best choice for guys that are already under 6-foot.

  17. J. D.

    July 16, 2008 at 12:21 pm

    I stopped wearing a jacket with shorts when I was twelve, or was it eleven? Maybe ten.

  18. josh y lola

    July 16, 2008 at 1:13 pm

    Oh, I don´t like shorts suit for men :-S buf

  19. Andrew

    July 16, 2008 at 1:13 pm

    If anyone knows where I could buy size 36 sportcoats, please let me know. For example, J.Crew’s size small is way too big. [email protected]

  20. whyioughtta

    July 16, 2008 at 1:14 pm

    Not loving the shoe choice of gent #3, but I think #1 works well because there’s some humour there.

    I just fear that we’ll now have a rash of less stylish men trying this look without as much success…eek.

    I suppose it was inevitable now that dress shorts are acceptable business wear for women.

  21. Dan Rousseau

    July 16, 2008 at 1:36 pm

    I’ve never been a shorts man (see ‘bird legs.’ but these shots might get my courage up.


  22. Anonymous

    July 16, 2008 at 2:05 pm

    I like the last guy a lot – I like when things that are not usually stylish, like a binder, can become stylish accessories (nice stripes!). I also like the soft pattern on his blazer, and his watch. Nicely done.

  23. tj

    July 16, 2008 at 2:06 pm

    For Greg in Boston:
    A lot will depend on your budget and personal style. Do you tend to favor classic looks, or do you want something more edgy?
    If you have some money to spend, and if you like a classic look, here is a place in the Boston area you can check out:
    If you want a place with a mix of classic and new styles you can go here:
    Both of the places mentioned above have tailors on staff for alterations. You can’t go wrong with either of these places (in my opinion).
    If you are on a budget, you can go to the places I mentioned above to get ideas, and then shop around at lower priced stores to find a similar look at a lower price.
    Good luck.

  24. Anonymous

    July 16, 2008 at 2:06 pm

    I love this look but its totally misleading to show it just on guys- i think it looks equally as good on women! In fact, i just bought the most amazing quarter-length sleeve blazer from shop and have paired it with everything from colorful long shorts to jean cut offs- fabulous.

  25. Benton

    July 16, 2008 at 2:17 pm

    the first guy owns it in my opinion
    classic look, with that great striped blazer to spice it up
    and i love his shoes
    A+ look!

  26. ricola

    July 16, 2008 at 2:22 pm

    Number one and Number three look great. Number two looks like he had no room in his bags for his jacket. Were it not so oppressively hot here in New Orleans, I’d probably experiment with this combo.

  27. sdg1844

    July 16, 2008 at 2:23 pm

    I’m a fan of the first 2 gents. Love the stripes in the jacket and the “spectator” like coloring of the boat shoe.

    Gent #2 is wonderful in a very “All American” Ralph Lauren kind of way.

  28. suzanne nelson

    July 16, 2008 at 2:40 pm

    i agree too. short suits are for 5 year olds or the catwalk while the right shorts and jacket can look so good on any age man. 1 and 2 are great, i love #1′s jacket, but #3 doesn’t quite hit the mark for me,it’s a bit random and the shoes feel too heavy.

  29. Ryan Brown

    July 16, 2008 at 2:50 pm

    Jorge from West Palm beach – I can only think of one man who can pull off the shorts suit…Bon Scott (AC/DC).

    these shorts and jackets look great.

  30. Anonymous

    July 16, 2008 at 3:30 pm

    I find the first guy the most charming. I think the fit is just so in all the right places and to me he has an air of confidence (perhaps arrogance?) that carries the clothes very well. I especially love his choice of jacket and shoes.

    The only thing I find interesting are the fabric of the second guys shorts and the fact that he has some some pretty nice legs. Other than that the hideous necklace and too trendy bags are a bit distracting.

    Lastly, the Japanese gone American Eccentric look has failed in the last picture. It’s too thrown together and the shoes are way too severe for his look. And maybe he should try a roomier short next time, no?


  31. Theo

    July 16, 2008 at 3:45 pm

    The striped jacket in the first picture is a great mix of pattern with a simple cut. The shoes are a wonderful addition.

  32. Karissa

    July 16, 2008 at 4:40 pm

    Love this in all but #3 — the rest of his look is too tailored for those shorts, down to the shoes. Looks as if he forgot his pants and his socks. But #1 and #2, yes!

  33. Ashley B.

    July 16, 2008 at 5:44 pm

    i really like the bottom style with the pencil thin shorts..the top striped jacket looks a little frumpy, but its probably just the angle

  34. style slicker

    July 16, 2008 at 6:05 pm

    i actually do like the look on the first pic.

  35. The Happiest Activist

    July 16, 2008 at 7:34 pm

    I like the third look, but the same rules that apply for women apply for men, and unless you’ve got decent legs, don’t wear outfits that scream “LOOK AT MY LEGS!”, which all of these do, simply by process of elimination (only skin visible…). There are definitely such things as nice legs on a guy and legs that are better under wraps…

  36. Gregor

    July 16, 2008 at 8:21 pm

    Those Band of Outsiders Sperry Top-Siders look awesome! Makes me wish I would have gotten a pair before they sold out!

  37. Anonymous

    July 16, 2008 at 8:52 pm

    Does anyone have information of the shoes of #2? I’d love a pair.

    [email protected]


  38. Adam

    July 16, 2008 at 9:39 pm

    loving the first bloke’s boat shoes, this summer’s “it” footwear especially paired with a pair of crisp cut cuffed shorts, perfect

  39. yibram palacios

    July 16, 2008 at 11:09 pm

    my shorts are much more shorter… and i love it. i wear it with Gucci black patent shoes or my pierre hardy sneackers but i really love how it looks whit my Dc.martens (!)

  40. Greg in Boston

    July 17, 2008 at 12:10 am

    For tj:

    Thanks, those look like great places to start.

  41. Anonymous

    July 17, 2008 at 12:40 am

    Shorts with or without jackets look great/modern/fresh on men .
    Scott You looked terrific recently in “madameFigaro” – shorts and a jacket.
    The article and the pictures were great – reminden me of why I love/need this site so much.

  42. Megan

    July 17, 2008 at 2:41 am

    Short suits? really? is that made for full grown men?

  43. nyc/caribbean ragazza

    July 17, 2008 at 3:29 am

    Love the cut of the first jacket.

  44. Anonymous

    July 17, 2008 at 3:48 am

    I think the preppy Bermudas work best here.

    – desertwind

  45. António Erre

    July 17, 2008 at 5:42 am

    Yes to the shorts suit.
    Best with a nice and muscled pair of legs!

  46. Designgod

    July 17, 2008 at 8:45 am

    I have been seeing these nautical belts everywhere. While there is something fun about them, I wish they would play a quieter role. In so many cases they BECOME the ensemble.

  47. Diana

    July 17, 2008 at 9:07 am

    I could imagine the first outfit…on the second gentleman.
    He has the right calves for the shorts.

  48. Anonymous

    July 17, 2008 at 9:37 am

    I’m ok with you Sart its depends of the own style.

  49. SpanishGent

    July 17, 2008 at 12:30 pm

    Great outfits, all of them! Perhaps I would choose different shoes in number one. I believe that they are called boat-shoes simply because they belong on a boat deck! but then, it is also a matter of taste.

  50. Miriam Parkman

    July 17, 2008 at 4:37 pm

    The first picture is elegant! Casual, but elegant. I think the shorts really works with the jacket. I love the navy feeling with the shoes and the stripes.

  51. Peter Breese

    July 17, 2008 at 11:14 pm

    something about the top image is just fantastic, it is as though you stole a shot from the 20′s (at least from the waist up). the colors are brilliant.

  52. Laura Pintos

    July 18, 2008 at 3:49 pm

    Like the second one.

  53. Imogen Quest

    July 18, 2008 at 5:40 pm

    love the shorts on men, in fact i much prefer the smart version of them Thom Browne style to the more relaxed slouchy shapeless surfer look. Shorts can be sharp. At the same time, loafers or boating shoes are such a no no for me – forgive me – just a personal opinion

  54. John and Beatrice

    July 20, 2008 at 4:42 am

    The shorts suit can most definitely work. Sometimes. In very specific locales. An all-inclusive resort in the Turks & Caicos? Yes. Also, it can be done ironically on an L-train platform in Brooklyn. We've seen it!

  55. Anonymous

    July 21, 2008 at 5:31 am

    sorryy, but i dont like men wear such shorts except casual places

  56. Anonymous

    July 21, 2008 at 5:34 am

    these men in shorts looks nice very fashionable, the best one is first

  57. YUME

    July 21, 2008 at 9:52 am

    Great look, this is something we like to wear as well, very masculine, and if worn by the right man, damn near neanderthal (but in a good way)
    Two Thumbs up

  58. Anonymous

    July 21, 2008 at 6:20 pm

    men in shorts always look ridiculous – as soon as age turns two digits shorts should be abandoned by any man, unless he wants to look like a little boy.

  59. Dan

    July 21, 2008 at 9:23 pm

    To whomever said “men in shorts always look ridiculous”, I would like to say that he or she is insane. I’m 50 years old and I look great in shorts. Pity the small minds.

  60. Anonymous

    July 23, 2008 at 1:44 pm

    also to the loathsome anonymous coward (from one to another) who croaked: “men in shorts always look ridiculous”

    … it was 94 degrees in manhattan the other day.

    so FUCK YOU.

  61. Anonymous

    July 27, 2008 at 12:02 pm

    fantastic shoes at the first picture!

  62. Anonymous

    July 27, 2008 at 3:03 pm

    The first two guys look pretty good. Number two is the best, very sporty looking. Number three doesn’t seem to have the right legs for it and the shorts are gross-way too tight.

  63. Nidya R. Wiguno

    October 12, 2008 at 5:25 am

    Anonymous said…

    The first two guys look pretty good. Number two is the best, very sporty looking. Number three doesn’t seem to have the right legs for it and the shorts are gross-way too tight.

    3:03 PM

    totally agree with it!

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